


Oh so fine.

by Edwardina



Category: Supernatural
Genre: Alternate Universe, Community: blindfold_spn, Crossdressing, Dirty Talk, Kink Meme, M/M
Language: English
Status: Completed
Published: 2009-08-28
Updated: 2009-08-28
Packaged: 2018-02-16 07:24:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,368
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2261010
Author URL: https://archiveofourown.org/users/Edwardina/pseuds/Edwardina
Summary: <blockquote class="userstuff">
              <p>prompt: Sam Wesson really wants into Dean Smith's pants. When he finally manages to get him to say yes, he's shocked to find out that he wears women's underwear under those pressed suits.</p>
            </blockquote>





	Oh so fine.

**Author's Note:**

> Written for blindfold_spn. Originally posted [here](http://community.livejournal.com/blindfold_spn/1037.html?thread=1728525#t1728525).

The day Sam Wesson beat his phone to death with an iron poker from Dean's fireplace and quit his position, something inside Dean finally cracked.

He went home that night, glugged from his master cleanse bottle, and sat on the end of his bed staring at his Ikea rug, wondering what Sam would think of him... if he really knew. Dean wondered that about everybody, really, from his boss to the interns that stood balancing piles of sandwiches and Starbucks cups in the elevator beside him to people who passed him on the street. What would they _think_ if they knew who Dean Smith really was inside?

Still, he pulled up Sam's file the next morning, called him up, sat through his voice mail picking up twice before Sam actually answered, sounding groggy. "'Lo?"

"So... you quit," said Dean.

There was a silence, then a sigh. "Yeah. Look, just - bill me for the phone. Take it out of my severance, whatever --"

"Well, the thing is, I've considered your options, and I'm not gonna let you quit," Dean replied in his best, brisk boss voice. "Yeah. I'm gonna need you here, so I expect to see you here tomorrow."

"You can't boss me around, Dean," Sam laughed on the other end. "I quit. I don't work for you anymore. I'm gonna --" A pause. "I'm gonna hunt."

"Yeah, well," Dean managed, his throat dry, "that's the thing. That's why you can't quit. That's why I'm gonna need you here. I think you gotta hang around. Help me out. Don't think I could do it on my own."

They must've sat there for a full minute before Sam spoke again, soft and dark. "You know what I'm talking about when I say you're not who you're supposed to be, don't you."

"Look," Dean began, discomfited, but Sam interrupted him.

"You feel it too, Dean, I know you do. We're supposed to do this! Together! Be a team! We're not supposed to be stuck in corporate hell, shoving --"

"Sam. Sam, you don't - you don't - know. Just... look, come back to work. Not gonna make you answer the phones. You need to be research and development, not tech support. We'll figure out what our next move is. We'll work on putting together some stuff we need. Get guns. Watch more Ghostfacers. See what there is out there. We gotta approach this whole thing right. We can't just go tearing off into the unknown, man. You know?"

"Yeah. Yeah... okay. I'll come back tomorrow," Sam agreed slowly.

"Superb!" said Dean, making Sam laugh. He was probably shaking his head.

So, Sam came back the very next day, yellow tech support polo stretched in place over his stupidly mammoth He-Man chest, and every single person in every tiny little tech support cubicle stared, but Sam didn't look like he gave a fuck as he sat himself down and put on his headset. Dean pretended to set down his brief case for a minute and mess with his morning paper just so he could watch, then continued to his office, where he sat, same as every other day, in his silk panties. His slacks hugged his ass and the panties felt awesome, so good and slippery on his balls. (Sometimes he worried about pantylines, but not as much as he worried about his bra showing through the layers of his wifebeater, undershirt, dress shirt, suspenders, and tie.) He tried not to feel guilty. After all, Sam was back with him and Sandover, so he wasn't alone. Not near as alone as he could be.

He tried not to rack up too much overtime, but Sam slid to his office before, during, and after every shift, bearing print-outs of news reports he'd Googled, stuff he thought Dean should research, information about guns and shooting ranges and bullet-making. He leaned over Dean's shoulder while they tried to sneak in watching anything ghost-related that they could find on the internet. Most of it was, as far as Dean could tell, bullshit, but Sam's instincts were always dead-on about leads that sounded promising, and Dean's adrenaline always got pumping when Sam's did.

"We need to go. We have to go!" Sam insisted, one Thursday morning. "Look, I Google Mapped it. It's just six hours away, five if we make good time. One day off. We just need one day off. We can take tomorrow off and make it there by the afternoon, then we'll have the whole weekend if we need it --"

"I really can't take a day off," Dean said, laughing uncomfortably, even though he ached to go, to get out there with Sam. He just couldn't. Something was rigidly holding him back. He just couldn't see himself checking into some grimy old motel with Sam, being able to sleep in that room, what he'd even pack in his suitcase. He didn't trust himself. He just didn't. He could do the job, sure, if Sam was there - but what else would he do?

"You can't keep me here forever, Dean," Sam groaned. "We have to get out there and do it sometime. Why not now?"

"I just --"

Dean had no real excuse.

"Y'know, I don't get it," Sam said, gesticulating wildly and stalking around Dean's desk, making him retreat automatically, back into a corner with unease flaring in his bones as Sam stepped right up to him, voice unnecessarily getting louder and louder. "I've seen you in action. I know you want to do this. We both know you can do it. What are you so afraid of, huh? Why are you so afraid to be yourself?"

"I'm not," Dean snapped back hoarsely. "Get out of my face, Sam."

"Oh, yeah, right. You're not in total denial. What're you afraid of, then? _Me_? Is it 'cause I know who you are even better than you do?"

"Oh, believe me," growled Dean. "You don't want to start on that with me. We - you and me - are strictly business, okay? I wanna do the job, okay? I wanna do the job. I don't wanna --" He stopped to swallow heavily, Sam's narrowed eyes making his stomach flip-flop. "Complicate... complicate things, okay. Don't do that. Don't act like you know me."

Dean stepped out from under Sam's hulking shadow.

"Better get back out there," he muttered, then spun in his place, because Sam had grabbed his shoulder and turned him back around so fast it hardly registered until it was too late and he was being kissed, a big broad palm on his cheek. Sam was taller than him; he wasn't used to his face being tilted like that, up to meet someone's mouth. That's all that clicked for a second. God, Sam was tall.

And he smelled unorthodoxically good. Simple. No thick, sharp designer cologne. None of the nervous sweat Dean always got a whiff of when people were called into his office. He just smelled clean, a little like aftershave and a little like soap, whatever detergent. Good. Masculine. Boyish.

Dean broke from him with a horrified gasp at that.

"No," found its way out of his mouth, but Sam didn't listen. He grasped both hands around Dean's face, pulled him in, kissed him stupid. And Dean let him. Just this once. Just - this once. Maybe it'd been coming from Day One and he'd just ignored it, denied it, but he'd always known Sam was like this, wanted this from him, and just once, he thought. Just once he'd see what it'd be like. To kiss a guy, or be kissed by one. Let Sam do it. Just let him get it out of his system...

But Sam backed him into the wall, bumping a piece of art crooked, not even close to hiding them behind the filing cabinet, and gasped in, hungry for air and for Dean's mouth to open for him, and his chest crushed against Dean's. If Dean could've died from the intensity of it, he would have. Just taken the easy way out and not feel how Sam's chest was pressing his back to the wall, pressing the elastic of his bra between them. He shrank, or tried to, and whimpered, but Sam's hands braced him, wanted him to kiss back. Dean let his tongue slip forward and was swept away from the heat of it, his tongue and Sam's.

"God, don't say you don't want this," Sam mouthed, somehow still kissing him around the words. "I know you do. I know you need me."

"You don't understand," Dean finally managed, but whatever he wanted to say, he lost it when Sam's hands slid down his chest, following the suspenders all the way down. His nipples were embarrassingly stiff against the itchy, teasing lace of his bra - couldn't Sam feel it? And then Sam's massive hands were on his ass - not just on it, but grabbing it, sliding deep like he was going to lift Dean by the insides of his thighs, fingers slipping long and tough and demanding over the elastic legholes of Dean's panties. Even with his shirt tucked in, Dean felt like he was naked to that grip and surrendered to babbling on the spot. "Sam. I'm not. I don't know why I do it. I can't help it. I need t --"

"I don't know why either, Dean. But I know. I just know," Sam panted, his breaths hot and puffing against Dean's face. "I've never wanted anything, anyone, so bad in my entire life. I've gotta fuck you. I wanna fuck you right over your desk. Show you all it's good for is propping you up while my dick's in you."

"Jesus Christ, what do you do all day, answer sex chat calls?" was all Dean could think to sputter out. He'd never been so red in his life.

The Xeroxes Sam had brought him fluttered off the desk as Sam, ginormously huge, strong Sam practically threw him on it, turned him over and shoved his face down onto his work calendar. And Dean didn't have time to think about how to warn Sam, not at all ( _Sam, just so you know, I wear women's underthings to work. I know, right? Got a whole collection. Today it's the black and purple lace. But, hey, don't worry. I'm not gay_ ) before Sam had unsnapped his suspenders, rucked up his dress shirt with animalistic pleasure, and jerked his pants down around his thighs.

"Oh my God," he heard Sam breathe, and mashed his own face punishingly against the desk. "Do you wear these every day?"

"Except Casual Fridays," Dean squeaked. "Then it's, uh... nothin'."

"Dean," Sam moaned. "All this time... in the elevator... when you're in meetings... when you're busting people's balls..."

Dean shuddered as Sam's warm hand cupped one of his ass cheeks, stroked him through the slinky, flimsy material, the silk purple and the lace black, like he was some slutty Elvira on Halloween or something, one of his most over-the-top sets that he loved because of the way it dipped on his stomach, the tiny silk bow it was adorned with perching on top of his junk like a pretty little present.

"Dean," Sam repeated slowly, his khaki-clad, casual hips doing a decidedly not-casual rub against Dean's ass - God, he could feel Sam's dick, all hard in them! Fuck, it was weird; fuck, it was hot, Sam practically fucking his panties through his own clothes. "This what you've been so afraid of? Anyone finding out about your sexy little panties?"

Oh, God. Dean moaned, and hard, mortified beyond belief but so, so turned on he couldn't even move. He just stood there, bent over his own desk, and let Sam's hand trail over him, feel up every inch of his panties, let his dick rub against his ass, helpless.

" _Me_ finding out about what you're wearin' under your bad-ass little boss-man cookie cutter suit?" Sam pressed on. "God, such pretty little panties, Dean. You like the way they make you feel?"

Against the desk, Dean's breath seemed to shake violently. "Yes."

"Yeah, I bet you do. Make you feel so fuckin' naughty, huh? Nobody knowin' how sexy you are under all this corporate bullshit, nobody knowin' who you really are, what you really want... except me. I knew you were different." Sam bent in over his back, hot, hot - hotter than Dean, somehow - and grinds his hips in, making Dean whimper against the desk. "Not even gonna take these little panties off you. Just slide 'em over... let me feel your hole..."

It'd be a lie for Dean to say he didn't ever get off playing with his own ass, especially at the end of a long workday in his bra and panties, but it was still a shock to feel someone else's finger sliding, wet and cool with lotion, right up into his hole. And it was weird to hear a phone ring down the hall and realize that any second, any fucking second, someone could walk by, peer through the cloudy glass of his office window a little too closely and see how Dean was getting bent over and fingered on his desk. Fucked, panties pulled aside, like he was the office slut getting a quickie in the copy room. He'd never been fucked, not like this.

Sam whispered to him, three fingers deep and fucking him dirtier and more personally than Dean had ever fucked any woman, "You want me to dick you right on your desk, don't you, Dean?"

"God, yes," Dean begged his calendar and the expense reports he was crushing in his fists tightly.

"Fuck your panties all wet?" Sam growled back.

"Please. Please, Sam. You're killin' me."

Sam's dick split Dean open like not even three fingers could've possibly prepared him for, pinned him to his desk, made him into the little bitch he was so fucking scared of being, but he didn't care anymore. Sam understood this. Sam understood him.

"Yeah, Dean. Gonna fuck your panties - God, look so hot on you. So bad, wearin' 'em to work, sittin' there talking prospects in your lacy little panties. Who you really are, isn't it?"

From Day One, Sam Wesson had somehow seen right through him.


End file.
